Holiday rentals in Cheltenham

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Top-rated holiday rentals in Cheltenham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Flat in Sandringham
4.97 out of 5 average rating, 33 reviews

One-Bedroom Terrace Apt. w/ Pool, Spa, Sauna & Gym

Welcome to the 3-1-9-1! Unwind in this light-filled, modern one-bedroom terrace apartment - perfect for a relaxed coastal escape or a bayside work-from-home stay. Enjoy a large private balcony, cosy hidden study, pool, spa, sauna and gym, plus easy access to beaches, cafés and public transport. Privately hosted in a secure residential building with dedicated parking, this calm, home-like space is ideal for couples, solo travellers, or professionals looking to slow down and enjoy bayside living.

Top guest favourite
Guest house in Sandringham
4.98 out of 5 average rating, 180 reviews

Delightful self contained cottage

The cottage is self contained and is a well designed space that accommodates a queen sized bed, bathroom and a separate study and is set in an enchanting cottage garden. The well equipped kitchen is in a separate space though part of the cottage and is accessed by its own door from the decking, so you don't have far to go. In the morning lorikeets and other wild birds come to feed and you will be awoken to the romantic sound of birdsong. During spring and summer the garden is at its loveliest.

Top guest favourite
A spacious bed is situated beside a stylish nightstand, featuring a decorative lamp and a vase of fresh orange roses. A soft throw is draped over the bed, complementing the light-colored bedding and brightening the serene bedroom atmosphere.
Flat in Highett
4.92 out of 5 average rating, 146 reviews

Bayside getaway, Impressive 1 bedroom apartment!

Comfortable apartment in Bayside Highett, a 2 min walk to train/bus stops, restaurants, bars & shops, 3 mins to major shopping centre, 10 mins to the beach & 30 mins to the city, conveniently positioned to explore Melbourne! Perfectly setup for couples & solo adventurers. As this is a whole apartment you have a fully equipped kitchen, private courtyard, laundry facilities and Netflix to be able to enjoy your stay. 24 hour check in with a key safe. Garage parking for small to medium sized car.

Superhost
A cozy interior features a spacious bed dressed in neutral tones, positioned next to a window displaying natural light. An adjoining kitchenette, equipped with modern appliances, is complemented by wooden accents. A comfortable seating area adds to the inviting atmosphere, accentuated by warm wooden flooring and soft lighting.
Guest house in Cheltenham
4.88 out of 5 average rating, 26 reviews

The Sanctuary Healing Retreat

Experience a luxury tranquil oasis designed for rejuvenation amidst nature. Unwind in top of the range Clearlight Sauna, refresh with an alfresco shower, and indulge in an open-air bath with magnesium and essential oils. Low EMF/TOX building biology build. Luxury Creswick bed. Alpaca doona and blanket. No smoking/vaping on property. Bus that goes to train station and Southland shopping centre or a 15 minute walk. 800m from IGA/chemist/post office. 7 minutes drive to Sandringham Beach.

Guest favourite
A cozy lounge area features two white, slipcovered sofas with patterned cushions, complemented by a central coffee table. A dining table with wooden chairs is positioned nearby, with a brick wall forming a rustic backdrop. Soft natural light filters through the window, illuminating the space.
Home in Black Rock
4.94 out of 5 average rating, 17 reviews

Rustic older home in a vibrant seaside village

An older style home with rustic features, located in the very heart of Black Rock in a quiet residential area. It is only a few metres walk away from a bus stop, the Black Rock shopping village and the beach. World renowned golf clubs are very close by. The house comprises lounge/dining room with an open fireplace, fully equipped kitchen, a sitting area, three bedrooms (one queen and two doubles), two bathrooms/toilets, laundry, fully enclosed backyard, on site parking. A home away from home!

Top guest favourite
A warmly decorated living space features a mix of vintage furnishings, including a green armchair and a vibrant dining table. Bright wall art adds character, while rich wooden accents and original floorboards create a cozy ambiance. Natural light streams in through the adjoining corridor.
Apartment in Beaumaris
5 out of 5 average rating, 108 reviews

Bayside on Keys

Welcome to a private, fully self contained, spacious and light 2 bedroom apartment set in a quiet bayside shopping village. Guests have 2 cafes, 2 restaurants, a Foodworks supermarket and bottle shop, tennis courts and a bowling club just steps away. There's plenty of free unlimited all day parking nearby. too. Located an easy 25km drive to the CBD, a stone’s throw from the cliffs of Port Phillip Bay, 3kms to Royal Melbourne Golf Course and a short walk to Ricketts Point Marine Sanctuary.

Top guest favourite
A modern bungalow is depicted with large sliding doors that open to a spacious outdoor area. A wooden dining table surrounded by chairs is visible on the patio, while the lush green lawn enhances the serene setting. Natural foliage lines the perimeter, providing privacy.
Guest house in Cheltenham
4.88 out of 5 average rating, 471 reviews

Bayside Bungalow

Backing onto the Victoria Golf Club, this stand alone bungalow is highly accessible to Victoria, Royal Melbourne, Sandringham and Cheltenham Golf clubs. It's a 10 minute walk to Cheltenham train station, close to shopping strips and a 5 minute drive to Southland Shopping Centre. It's modern, private, with Japanese screens allowing for natural light and block out blinds for full privacy. It is comfortable in a beautiful backyard setting with, its own access and a 3-minute drive to the beach.

Top guest favourite
A bright living space features a light-toned sofa adorned with cushions, complemented by a round ottoman in soft pink. A wooden TV unit holds a flat-screen television, while large windows allow natural light to fill the room, creating an inviting atmosphere.
Home in Mentone
4.97 out of 5 average rating, 79 reviews

Cosy Seaside Retreat - Charming Unit by the Beach

Discover a charming retreat just 2km from Mentone's pristine beaches. This cosy 2-storey unit boasts a fully equipped kitchen, offering a perfect blend of comfort and convenience. Immerse yourself in a relaxing getaway, surrounded by the best south-east Melbourne has to offer! Local shops, restaurants and public transportation within walking distance and a mere 35 minutes from the Melbourne CBD. This location is a great central base for anyone wanting to explore the south-east of Victoria.

Guest favourite
A spacious living area features two comfortable leather recliners and a cozy sofa, arranged around a modern coffee table. A large wall-mounted television is positioned across from the seating, and natural light is invited through large windows, brightening the room.
Home in Highett
4.97 out of 5 average rating, 39 reviews

Highett Charm - Spacious modern 3 bedroom Unit

This 3 bedroom unit is spacious enough for a family or cosy enough for a couple. It is a short walk to the center of Highett and train station. Southland Shopping Centre is only a 3min drive away for all of your shopping needs. A spacious undercover outdoor space offers guests the opportunity to cook up a storm on the BBQ provided. Ducted heating and reverse cycle cooling for your comfort. Smart TV's are installed in all rooms. 1 undercover and one additional car space is available.

Top guest favourite
An open-plan kitchen area is highlighted by modern cabinetry and a sleek countertop. Three wooden stools are positioned at the counter. Large windows allow natural light to illuminate the space, which features a cool blue backsplash and essential kitchen appliances.
Tiny home in Cheltenham
5 out of 5 average rating, 17 reviews

New bungalow in Cheltenham.

Newly built, one bedroom bungalow in Cheltenham at the back of a family home. The bungalow has its own front door access. Queen sized bed, large bathroom and open plan living area with a full kitchen. 300m to Cheltenham train station, shops and restaurants. 150m to all day parking. 1.5km to Southland shopping centre. 2km to the beach. The front door is off a driveway access at the back of the whole property and the back door opens onto the garden of our family home with children.

Superhost
Flat in Cheltenham
4.75 out of 5 average rating, 16 reviews

Cheltenham Gem | Ocean Views | Fits a Family of 6

With ocean glimpses and open skies, this bright 2-bed apartment sleeps 6 comfortably. Large balcony accessible from lounge and second bedroom. Queen bed, 2 singles, sofa bed. Free WiFi, A/C, fully equipped kitchen, secure free parking. 2-min walk to Cheltenham station, direct to CBD. Steps from Cheltenham & Victoria Golf Clubs, Kingston Centre (Monash Health), Westfield Southland & Kingston City Council. Keys via secure coded lockbox — arrive any time. Superhost, rated 4.75★

Superhost
A well-appointed bedroom contains a spacious bed with decorative pillows and a cozy throw. Nightstands with lamps are located on either side. A small desk and chair are visible in the background, accompanied by framed wall art. Natural light enters through a window with minimal coverings.
Serviced apartment in Sandringham
4.85 out of 5 average rating, 110 reviews

One Bedroom Premium Apartment

One Bedroom Premium Apartments include: - One spacious bedroom with King/Queen sized bed - Bathroom with shower & hairdryer - Fully equipped kitchen facilities - Open plan living and dining with 50” Crystal LED UHD 4K Smart TV - Private Laundry equipped with iron & ironing board - Private balcony with outdoor furniture - Individually controlled ducted heating and air conditioning - Bluetooth clock/radio - Direct dial telephone - Complimentary high speed Wifi Internet

Popular amenities for Cheltenham holiday rentals

When is the best time to visit Cheltenham?

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Avg. price$131 SGD$129 SGD$134 SGD$119 SGD$102 SGD$101 SGD$109 SGD$125 SGD$114 SGD$112 SGD$120 SGD$133 SGD
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Frequently Asked Questions

  • How much does it cost to stay in serviced apartment rentals in Cheltenham?

    Experience the best of Cheltenham with our serviced apartment rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Cheltenham?

    Yes! Work meets play with ease at over 60 vacation rentals in Cheltenham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Cheltenham?

    Four-legged friends are welcome in Cheltenham. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there Cheltenham vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Cheltenham, available on Airbnb. Make a splash and soak up the sun in style!

  • Do serviced apartment rentals in Cheltenham have air conditioning?

    Absolutely! We offer over 10 serviced apartment rentals with air conditioning in Cheltenham. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Cheltenham have a kitchen?

    Absolutely! We offer over 40 apartment rentals with a kitchen in Cheltenham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cheltenham have wifi?

    Absolutely! We offer over 60 house rentals with wifi in Cheltenham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cheltenham have free parking?

    Absolutely! We offer over 50 house rentals with free parking in Cheltenham. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Cheltenham?

    Cheltenham has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Apartment Rentals in Cheltenham?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with wifi, over 40 homes with air conditioning, over 40 homes with a kitchen, over 30 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Cheltenham

  • Total holiday rentals

    Explore 150 holiday rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,430 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    130 of Cheltenham holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Cheltenham rentals

  • 4.8 Average rating

    Cheltenham stays are highly rated by guests – averaging 4.8 out of 5!

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